201232-82-8Relevant academic research and scientific papers
Bi(OTf)3 as novel and efficient catalyst for the stereoselective synthesis of C-pseudoglycals
Yadav,Reddy,Reddy, K. Srinivasa,Chandraiah,Sunitha
, p. 2523 - 2526 (2004)
D-Glycals undergo smoothly allylic rearrangement with allyltrimethylsilane and trimethylsilyl cyanide in the presence of catalytic amount of bismuth triflate to afford the corresponding 2,3-unsaturated allyl glycosides and glycosyl cyanides in excellent y
Zirconium(IV) chloride catalyzed synthesis of 2,3-unsaturated C, N, O, S, and heteroaromatic glycosylation in the ferrier rearrangement
Swamy, Navath,Srinivasulu, Masuna,Reddy, Thummalapally,Goud, Thirumani,Venkateswarlu, Yenamandra
, p. 435 - 441 (2004)
The reaction of tri-O-acetyl-D-glucal with nucleophiles to afford the corresponding 2,3-unsaturated glycopyranosides in excellent yields by zirconium(IV) chloride in acetonitrile at ambient temperature has been demonstrated. Copyright
Gd(OTf)3 catalyzed preparation of 2,3-unsaturated O-, S-, N-, and C-pyranosides from glycals by Ferrier Rearrangement
Chen, Peiran,Su, Jie
supporting information, p. 84 - 94 (2015/12/23)
By using Gd(OTf)3 as the catalyst, synthesis of 2,3-unsaturated-glycosides has been performed by Ferrier Rearrangement. A series of 2,3-unsaturated O-, S-, N-, and C-glycosides were obtained from 3,4,6-tri-O-acetyl-d-glucal, 3,4,6-tri-O-benzyl-d-glucal, and 3,4-di-O-acetyl-l-rhamnal under mild reaction conditions in good yields and high anomeric selectivities.
Ruthenium catalyzed synthesis of 2,3-unsaturated C-glycosides from glycals
Srinivas, Batthula,Reddy, Thurpu Raghavender,Kashyap, Sudhir
, p. 86 - 92 (2015/02/19)
A highly efficient and convenient C-glycosylation method was developed using ruthenium(III) chloride for the synthesis of 2,3-unsaturated C-glycosides. Various nucleophiles such as allyl trimethylsilane, triethylsilane, trimethylsilyl cyanide, trimethylsi
A mild and efficient Zn-catalyzed C-glycosylation: Synthesis of C(2)-C(3) unsaturated C-linked glycopyranosides
Reddy, Thurpu Raghavender,Rao, Dodla Sivanageswara,Kashyap, Sudhir
, p. 28338 - 28343 (2015/04/14)
A highly efficient C-glycosylation method was developed by using catalytic Zn(OTf)2 for the synthesis of 2,3-unsaturated C-glycosides. The scope of the protocol was well illustrated with different substituted glycals and nucleophiles comprising
Diastereoselective synthesis of the C29-C41 fragment of karlotoxin 2
Reddy, D. Srinivas,Gaddam, Janardhan,Devunuri, Nagaraju,Mohapatra, Debendra K.
, p. 4299 - 4301 (2015/06/22)
A highly diastereoselective synthesis of the C29-C41 fragment of karlotoxin 2 (KmTx2) is described by employing regio-selective epoxide opening, our own developed domino isomerization followed by C-O and C-C bond formation reaction and chelation-controlled Grignard reaction as key steps. The synthesis involves installation of seven stereocenters present in the C29-C41 fragment of karlotoxin 2.
Efficient carbon-Ferrier rearrangement on glycals mediated by ceric ammonium nitrate: Application to the synthesis of 2-deoxy-2-amino-C-glycoside
Ansari, Alafia A.,Reddy, Y. Suman,Vankar, Yashwant D.
supporting information, p. 300 - 306 (2014/03/21)
A carbon-Ferrier rearrangement on glycals has been performed by using ceric ammonium nitrate to obtain products in moderate to good yields with high selectivity. The versatility of this method has been demonstrated by applying it to differently protected
"Design" of boron-based compounds as pro-nucleophiles and co-catalysts for indium(I)-catalyzed allyl transfer to various Csp 3-type electrophiles
Dao, Hai Thanh,Schneider, Uwe,Kobayashi, Shu
experimental part, p. 2522 - 2529 (2012/07/13)
We have recently uncovered a general indium(I)-catalyzed method for allylations and propargylation of acetals and ketals with a water- and air-stable allyl boronate. By using a more reactive allyl borane, we have successfully extended this methodology to the more challenging C-C coupling with ethers. Herein, we report an improved methodology for the indium(I)-catalyzed allylation of acetals and ethers, through combination of the allyl boronate with a commercially available "hard" Lewis acid, B-methoxy-9-BBN (BBN=borabicyclo[3.3.1]nonane), as an effective co-catalyst. Significantly, our work highlights for the first time the correlation between the Lewis acidity of "electrophilic" boron-based compounds and their " nucleophilic" reactivity in Csp3-Csp3 couplings, catalyzed by a "soft" low-oxidation main group metal. In addition, we also report several applications of these methodologies to the selective synthesis of various carbohydrate derivatives. Copyright
Direct one-pot conversion of acylated carbohydrates into their alkylated derivatives under heterogeneous reaction conditions using solid NaOH and a phase transfer catalyst
Madhusudan, Soni Kamlesh,Agnihotri, Geetanjali,Negi, Devendra S.,Misra, Anup Kumar
, p. 1373 - 1377 (2007/10/03)
A convenient one-pot protocol for the direct conversion of acyl-protected carbohydrates into their alkylated counterparts has been developed by using alkyl halides in the presence of solid sodium hydroxide and a phase transfer catalyst. These economically
Synthesis of α- and β-C-Aryl Δ2-Glycopyranosides from p-tert-Butylphenyl Δ2-Glycopyranosides via Grignard Reagents
Moineau, Christophe,Bolitt, Véronique,Sinou, Denis
, p. 582 - 591 (2007/10/03)
Treatment of p-tert-butylphenyl 4,6-di-O-benzyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (1aα) or the 4,6-di-O-(tert-butyldimethylsilyl) analogue (1bα) with various functionalized arylmagnesium bromides in the presence of a catalytic amount of PdCl2(dppf) at 25°C in THF afforded the corresponding unsaturated C-arylglycosides 2-14 having the α-configuration in quite good yields. Benzyl-, allyl-, and vinylmagnesium bromides gave also the corresponding unsaturated α-C-glycosides 15-18, although in lower yields. When the same reaction was performed in the presence of NiCl2(dppe) as the catalyst at -40°C, only the formation of the corresponding unsaturated C-arylglycosides having the β-configuration was observed. As expected, reaction of phenylmagnesium bromide with p-tert-butylphenyl 4,6-di-O-benzyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside (1aβ) in the presence of NiCl2(dppe) gave only the unsaturated β-C-phenylglycoside 2aβ, while palladium-catalyzed reaction led to the preponderant formation of C-phenylglycoside 2aα. Reaction of PhMgBr with p-tert-butylphenyl 4-O-benzyl-2,3,6-trideoxy-α-L-erythro-hex-2-enopyranoside (20) afforded stereospecifically the unsaturated α- and β-C-phenylglycoside 25 in the presence of PdCl2-(dppf) and NiCl2(dppe), respectively.
